5-(benzo[d]-[1,3]dioxo-5-yl)-2-diazohexane-1,3-dione | 1318759-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d]-[1,3]dioxo-5-yl)-2-diazohexane-1,3-dione
• 英文别名: 5-(1,3-Benzodioxol-5-yl)-2-diazo-1,3-cyclohexanedione；5-(1,3-benzodioxol-5-yl)-2-diazocyclohexane-1,3-dione
• CAS: 1318759-84-0
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: ZTGXUZYZJXELAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzo[d]-[1,3]dioxo-5-yl)-2-diazohexane-1,3-dione 在 tris(triphenylphosphine)ruthenium(II) chloride 、 草酰溴 作用下， 以 氟苯 为溶剂， 反应 10.0h， 以62%的产率得到3-(benzo[d][1,3]dioxol-5-yl)-5-bromophenol
  参考文献：
  名称：

  钌（II）催化的重氮二羰基化合物制备各种α，β-和β，β-二卤代烯酮的方案

  摘要：

  AbstractEfficient one‐step syntheses of α,β‐ and β,β‐dihaloenones were achieved by ruthenium(II)‐catalyzed reactions between cyclic or acyclic diazodicarbonyl compounds and oxalyl chloride or oxalyl bromide in moderate to good yields. This methodology offers several significant advantages, which include ease of handling, mild reaction conditions, one‐step reaction, and the use of an effective and non‐toxic catalyst. The synthesized compounds were further transformed into highly functionalized novel molecules bearing aromatic rings on the enone moiety using the Suzuki reaction.magnified image

  DOI：

  10.1002/adsc.201400348
• 作为产物：
  描述：

  5-[3,4-(甲二氧基)苯基]-1,3-环己二酮 在 sulfonyl azide 作用下， 生成 5-(benzo[d]-[1,3]dioxo-5-yl)-2-diazohexane-1,3-dione
  参考文献：
  名称：

  通过RuII催化的重氮二羰基化合物的[3+2]环加成反应区域选择性合成高度官能化的呋喃

  摘要：

  描述了一种从容易获得的环状和非环状重氮二羰基化合物和末端炔烃中 RuII 催化区域选择性合成高度官能化呋喃的新方法。设计的协议为通过强大的级联过程构建各种不同的呋喃衍生物提供了一种直接的方法，包括钌卡宾的形成、环丙烯化、开环复分解和环化。

  DOI：

  10.1002/ejoc.201402067

文献信息

• Ruthenium catalyzes the synthesis of γ-butenolides fused with cyclohexanones
  作者：Raju S. Thombal、Seoung-Tae Kim、Mu-Hyun Baik、Yong Rok Lee

  DOI：10.1039/c9cc00101h

  日期：——

  Ruthenium(II)-catalyzed reactions of cyclic diazodicarbonyl compounds with β-ketoamides for chemo- and stereoselective construction of cyclohexanone-fused γ-butenolides are described. This study represents the first example of the addition of an enol substrate which is formed by the tautomerization of the β-ketoamides to the electrophilic carbene center for unusual cyclization through amide cleavage

  描述了钌（II）催化的环状重氮二羰基化合物与β-酮酰胺的化学和立体选择性构建，环己酮稠合的γ-丁烯内酯。这项研究代表了添加一个烯醇底物的第一个例子，该底物是通过将β-酮酰胺互变异构化到亲电子卡宾中心形成的，以通过酰胺裂解实现异常环化。组合的实验和计算研究揭示了有利于异常环形成反应的机理途径，而不是一般的羰基叶立德中间体参与产物生成的机理。
• AgBF₄/[Bmim]BF₄-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans
  作者：Likai Xia、Yong-Rok Lee、Sung-Hong Kim、Won-Seok Lyoo

  DOI：10.5012/bkcs.2011.32.5.1554

  日期：2011.5.20

  A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF/[Bmim]BF-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.

  通过环状重氮二羰基化合物与苯乙烯和乙酸乙烯酯的反应，实现了一种新型高效的二氢呋喃环上具有多种取代基的 2,3-二氢呋喃的合成方法。关键策略是 AgBF/[Bmim]BF 催化的 [3+2] 环加成。合成的具有乙酸根的二氢呋喃进一步转化为相应的 3-酰基呋喃。
• In( <scp>III</scp> )‐Catalyzed <scp> <i>O</i> ‐Annulation </scp> of Cyclic Diazodicarbonyls with <scp>2‐Naphthol</scp> , <scp>6‐Quinolinol</scp> , <scp>β‐Tetralone</scp> , and <scp>9‐Phenanthrol</scp> to Access Diverse Benzochromones
  作者：Shizuka Mei Bautista Maezono、Hari Datta Khanal、Priyanka Chaudhary、Ga Eul Park、Yong Rok Lee

  DOI：10.1002/bkcs.12207

  日期：2021.3

  2‐naphthols, 6‐quinolinol, β‐tetralone, and 9‐phenanthrol is developed. This novel synthetic strategy paves a facile and desired access to diverse and functionalized benzochromones. This imperative protocol involves domino carbene generation, ketene formation through Wolff‐rearrangement, nucleophilic addition, H‐migration, intramolecular cyclization, and elimination of water.

  在（III）催化下，环状重氮二羰基化合物与2-萘酚，6-喹啉醇，β-四氢萘酮和9-菲咯啉的O环化反应得以发展。这种新颖的合成策略为轻松获得各种功能化的苯并色酮提供了所需的途径。该命令性协议涉及多米诺卡宾的产生，通过Wolff重排形成烯酮，亲核加成，H迁移，分子内环化和除水。
• Efficient One-Pot Synthesis of Multi-Substituted Dihydrofurans by Ruthenium(II)-Catalyzed [3+2] Cycloaddition of Cyclic or Acyclic Diazodicarbonyl Compounds with Olefins
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1002/adsc.201300245

  日期：2013.8.12

  AbstractRuthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate Ru(PPh3)3Cl2/[Bmim]BF4}‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.magnified image